# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers
# This journal is © The Partner Organisations 2013

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_sa2926

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Br N3 O'
_chemical_formula_sum            'C16 H16 Br N3 O'
_chemical_formula_weight         346.23
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.466(6)
_cell_length_b                   12.4249(8)
_cell_length_c                   13.3396(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1568.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5423
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    2.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5742
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12305
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3577
_reflns_number_gt                3484
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'


_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0312P)^2^+0.3509P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.011(8)
_refine_ls_number_reflns         3577
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.0677
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.58133(3) 0.791782(18) 0.192322(17) 0.03731(8) Uani 1 1 d . . .
O1 O 0.4811(2) 0.38396(13) 0.51602(13) 0.0383(4) Uani 1 1 d . . .
H1 H 0.4962 0.3227 0.5405 0.057 Uiso 1 1 calc R . .
N1 N 0.4533(2) 0.57970(14) 0.76707(14) 0.0268(4) Uani 1 1 d . . .
N2 N 0.4730(2) 0.68231(14) 0.79767(15) 0.0335(4) Uani 1 1 d . . .
N3 N 0.4617(2) 0.68628(15) 0.89503(15) 0.0333(5) Uani 1 1 d . . .
C1 C 0.6019(3) 0.44975(16) 0.53001(16) 0.0275(5) Uani 1 1 d . . .
H1A H 0.6884 0.4051 0.5185 0.033 Uiso 1 1 calc R . .
C2 C 0.6040(3) 0.49181(17) 0.63963(16) 0.0262(5) Uani 1 1 d . . .
H2 H 0.6053 0.4273 0.6844 0.031 Uiso 1 1 calc R . .
C3 C 0.7341(3) 0.5583(2) 0.66515(18) 0.0359(5) Uani 1 1 d . . .
H3A H 0.7340 0.6244 0.6252 0.054 Uiso 1 1 calc R . .
H3B H 0.8193 0.5165 0.6501 0.054 Uiso 1 1 calc R . .
H3C H 0.7327 0.5767 0.7366 0.054 Uiso 1 1 calc R . .
C4 C 0.4666(3) 0.55254(19) 0.66131(17) 0.0295(5) Uani 1 1 d . . .
H4A H 0.4643 0.6194 0.6210 0.035 Uiso 1 1 calc R . .
H4B H 0.3853 0.5075 0.6409 0.035 Uiso 1 1 calc R . .
C5 C 0.4315(2) 0.51442(16) 0.84741(15) 0.0236(4) Uani 1 1 d . . .
C6 C 0.4103(3) 0.40294(16) 0.85811(16) 0.0271(4) Uani 1 1 d . . .
H6 H 0.4071 0.3558 0.8021 0.032 Uiso 1 1 calc R . .
C7 C 0.3946(3) 0.36661(18) 0.95452(19) 0.0330(5) Uani 1 1 d . . .
H7 H 0.3808 0.2918 0.9654 0.040 Uiso 1 1 calc R . .
C8 C 0.3979(3) 0.43592(19) 1.03829(17) 0.0324(5) Uani 1 1 d . . .
H8 H 0.3857 0.4067 1.1035 0.039 Uiso 1 1 calc R . .
C9 C 0.4185(3) 0.54502(17) 1.02743(16) 0.0301(4) Uani 1 1 d . . .
H9 H 0.4206 0.5919 1.0836 0.036 Uiso 1 1 calc R . .
C10 C 0.4362(2) 0.58341(16) 0.92983(16) 0.0255(4) Uani 1 1 d . . .
C11 C 0.5968(3) 0.53811(16) 0.45113(15) 0.0250(4) Uani 1 1 d . . .
C12 C 0.7200(2) 0.58816(17) 0.41894(17) 0.0273(5) Uani 1 1 d . . .
H12 H 0.8077 0.5690 0.4487 0.033 Uiso 1 1 calc R . .
C13 C 0.7169(2) 0.66600(18) 0.34370(17) 0.0282(5) Uani 1 1 d . . .
H13 H 0.8015 0.7001 0.3224 0.034 Uiso 1 1 calc R . .
C14 C 0.5887(3) 0.69274(15) 0.30058(15) 0.0274(4) Uani 1 1 d . . .
C15 C 0.4645(3) 0.64549(19) 0.33237(18) 0.0325(5) Uani 1 1 d . . .
H15 H 0.3768 0.6656 0.3034 0.039 Uiso 1 1 calc R . .
C16 C 0.4698(3) 0.56779(19) 0.40766(18) 0.0306(5) Uani 1 1 d . . .
H16 H 0.3848 0.5346 0.4295 0.037 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.05036(15) 0.03372(12) 0.02784(12) 0.01203(9) -0.00032(11) -0.00061(11)
O1 0.0593(11) 0.0233(8) 0.0323(9) 0.0031(7) -0.0044(8) -0.0089(8)
N1 0.0333(11) 0.0233(9) 0.0238(9) 0.0003(7) 0.0009(8) 0.0027(7)
N2 0.0472(11) 0.0212(8) 0.0322(11) 0.0009(8) 0.0021(9) 0.0043(7)
N3 0.0466(12) 0.0237(9) 0.0297(10) -0.0019(7) 0.0010(8) 0.0036(8)
C1 0.0379(13) 0.0208(9) 0.0240(10) 0.0028(8) 0.0024(10) 0.0025(9)
C2 0.0335(12) 0.0244(9) 0.0206(10) 0.0031(8) 0.0002(9) 0.0027(9)
C3 0.0340(13) 0.0438(13) 0.0301(13) 0.0028(10) -0.0007(10) -0.0021(11)
C4 0.0363(13) 0.0314(11) 0.0208(11) 0.0012(8) -0.0023(9) 0.0050(9)
C5 0.0223(10) 0.0242(9) 0.0242(10) -0.0002(8) 0.0007(9) 0.0020(8)
C6 0.0267(11) 0.0244(9) 0.0301(11) -0.0044(8) 0.0013(10) -0.0012(9)
C7 0.0342(13) 0.0246(10) 0.0402(13) 0.0032(9) 0.0051(11) -0.0028(9)
C8 0.0346(13) 0.0359(11) 0.0266(11) 0.0070(9) 0.0046(10) 0.0026(10)
C9 0.0347(12) 0.0309(10) 0.0249(10) -0.0024(8) -0.0001(11) 0.0049(11)
C10 0.0285(11) 0.0220(9) 0.0260(10) -0.0014(8) -0.0013(9) 0.0039(8)
C11 0.0358(12) 0.0213(9) 0.0178(9) 0.0006(7) 0.0011(9) 0.0034(9)
C12 0.0315(12) 0.0272(10) 0.0232(10) 0.0009(9) 0.0018(9) 0.0065(8)
C13 0.0319(12) 0.0271(10) 0.0258(11) 0.0011(8) 0.0043(9) -0.0021(9)
C14 0.0404(11) 0.0223(9) 0.0194(9) 0.0031(8) 0.0013(10) 0.0007(9)
C15 0.0330(12) 0.0337(12) 0.0309(13) 0.0071(9) -0.0046(9) 0.0012(9)
C16 0.0360(13) 0.0305(11) 0.0253(11) 0.0050(9) 0.0003(10) -0.0018(9)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C14 1.8986(19) . ?
O1 C1 1.418(3) . ?
O1 H1 0.8400 . ?
N1 N2 1.352(3) . ?
N1 C5 1.360(3) . ?
N1 C4 1.456(3) . ?
N2 N3 1.304(3) . ?
N3 C10 1.381(3) . ?
C1 C11 1.521(3) . ?
C1 C2 1.553(3) . ?
C1 H1A 1.0000 . ?
C2 C3 1.521(3) . ?
C2 C4 1.531(3) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.395(3) . ?
C5 C6 1.407(3) . ?
C6 C7 1.371(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.411(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(3) . ?
C9 H9 0.9500 . ?
C11 C16 1.385(4) . ?
C11 C12 1.390(3) . ?
C12 C13 1.394(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(3) . ?
C15 C16 1.394(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
N2 N1 C5 110.22(18) . . ?
N2 N1 C4 119.95(19) . . ?
C5 N1 C4 129.68(18) . . ?
N3 N2 N1 108.97(18) . . ?
N2 N3 C10 108.30(18) . . ?
O1 C1 C11 107.41(18) . . ?
O1 C1 C2 109.15(19) . . ?
C11 C1 C2 114.12(17) . . ?
O1 C1 H1A 108.7 . . ?
C11 C1 H1A 108.7 . . ?
C2 C1 H1A 108.7 . . ?
C3 C2 C4 112.19(19) . . ?
C3 C2 C1 113.81(19) . . ?
C4 C2 C1 109.44(18) . . ?
C3 C2 H2 107.0 . . ?
C4 C2 H2 107.0 . . ?
C1 C2 H2 107.0 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C2 111.76(18) . . ?
N1 C4 H4A 109.3 . . ?
C2 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C2 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
N1 C5 C10 104.46(17) . . ?
N1 C5 C6 133.6(2) . . ?
C10 C5 C6 122.0(2) . . ?
C7 C6 C5 115.8(2) . . ?
C7 C6 H6 122.1 . . ?
C5 C6 H6 122.1 . . ?
C6 C7 C8 122.6(2) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 116.8(2) . . ?
C8 C9 H9 121.6 . . ?
C10 C9 H9 121.6 . . ?
N3 C10 C5 108.03(19) . . ?
N3 C10 C9 130.6(2) . . ?
C5 C10 C9 121.41(19) . . ?
C16 C11 C12 118.69(19) . . ?
C16 C11 C1 120.6(2) . . ?
C12 C11 C1 120.6(2) . . ?
C11 C12 C13 121.0(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 119.0(2) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 121.13(19) . . ?
C15 C14 Br1 118.54(17) . . ?
C13 C14 Br1 120.29(17) . . ?
C14 C15 C16 119.0(2) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C11 C16 C15 121.1(2) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 N3 -1.4(3) . . . . ?
C4 N1 N2 N3 -177.3(2) . . . . ?
N1 N2 N3 C10 1.0(3) . . . . ?
O1 C1 C2 C3 176.61(18) . . . . ?
C11 C1 C2 C3 -63.2(3) . . . . ?
O1 C1 C2 C4 -57.0(2) . . . . ?
C11 C1 C2 C4 63.2(3) . . . . ?
N2 N1 C4 C2 105.8(2) . . . . ?
C5 N1 C4 C2 -69.3(3) . . . . ?
C3 C2 C4 N1 -61.3(2) . . . . ?
C1 C2 C4 N1 171.34(18) . . . . ?
N2 N1 C5 C10 1.1(2) . . . . ?
C4 N1 C5 C10 176.6(2) . . . . ?
N2 N1 C5 C6 -177.8(3) . . . . ?
C4 N1 C5 C6 -2.3(4) . . . . ?
N1 C5 C6 C7 178.8(2) . . . . ?
C10 C5 C6 C7 0.0(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
N2 N3 C10 C5 -0.3(3) . . . . ?
N2 N3 C10 C9 178.8(3) . . . . ?
N1 C5 C10 N3 -0.5(2) . . . . ?
C6 C5 C10 N3 178.6(2) . . . . ?
N1 C5 C10 C9 -179.7(2) . . . . ?
C6 C5 C10 C9 -0.7(4) . . . . ?
C8 C9 C10 N3 -178.3(2) . . . . ?
C8 C9 C10 C5 0.7(4) . . . . ?
O1 C1 C11 C16 23.3(3) . . . . ?
C2 C1 C11 C16 -97.9(3) . . . . ?
O1 C1 C11 C12 -154.6(2) . . . . ?
C2 C1 C11 C12 84.3(3) . . . . ?
C16 C11 C12 C13 -0.6(3) . . . . ?
C1 C11 C12 C13 177.3(2) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 1.5(3) . . . . ?
C12 C13 C14 Br1 -176.12(16) . . . . ?
C13 C14 C15 C16 -1.5(3) . . . . ?
Br1 C14 C15 C16 176.13(17) . . . . ?
C12 C11 C16 C15 0.6(3) . . . . ?
C1 C11 C16 C15 -177.3(2) . . . . ?
C14 C15 C16 C11 0.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N3 0.84 1.94 2.781(3) 175.9 3_646

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 965694'